Sodium Methoxide → HCID 86724817, compound

HRID 1525583Notes

Reaction equation

HRID 1525583 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][C@@H:14]([CH3:28])[C@@H:15]([CH3:27])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].C[O-].[Na+].[N+:32]([C:35]1[N:36]=[CH:37][NH:38][CH:39]=1)([O-:34])=[O:33]>>[CH3:26][O:25][C:19]1[CH:18]=[C:17]([CH2:16][C@H:15]([CH3:27])[C@H:14]([CH3:28])[CH2:13][C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH2:3][CH2:2][N:38]3[CH:39]=[C:35]([N+:32]([O-:34])=[O:33])[N:36]=[CH:37]3)[CH:6]=2)[CH:22]=[CH:21][C:20]=1[O:23][CH3:24]

Participants

4

Reactant 3

HCID 10942334Sodium MethoxideHCID 86724818HCID 86724818, compoundHCID 178526856HCID 178526856, compound

Product 1

HCID 86724817HCID 86724817, compoundYield 61.2%

Procedure

The Standard Procedure 2 was followed by use of 5a (58.2 mg, 0.129 mmol, 1.0 equiv), sodium methoxide (15.4 mg, 0.285 mmol, 2.2 equiv), and 4-nitroimidazole (6a, 29.3 mg, 0.259 mmol, 2.0 equiv). After workup and purification with column chromatography (80% EtOAc in hexanes as eluant), 7a (38.1 mg, 0.0789 mmol) was obtained in 61% yield as white solids: mp (recrystallized from methanol) 80.4-81.0° C.; 1H NMR (CDCl3, 400 MHz) δ 0.79 (d, J=6.8 Hz, 3H, CH3), 0.83 (d, J=6.4 Hz, 3H, CH3), 1.59-1.76 (m, 2H, 2×CH), 2.17-2.35 (m, 2H, 2×ArCH), 2.67-2.71 (m, 2H, 2×ArCH), 3.82 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.18-4.22 (m, 2H, CH2N), 4.36 (t, J=4.6 Hz, 2H, CH2O), 6.51 (s, 1H, ArH), 6.65-6.68 (m, 2H, 2×ArH), 6.73-6.78 (m, 3H, 3×ArH), 7.60 (s, 1H, nitroimidazole C5-H), 8.12 (s, 1H, nitroimidazole C2-H); 13C NMR (CDCl3, 100 MHz) δ 16.06, 16.20, 38.25, 38.95, 39.04, 39.06, 47.92, 55.77, 55.81, 55.92, 68.08, 111.17, 111.66, 112.45, 115.50, 120.60, 120.90, 123.10, 134.34, 134.58, 136.56, 146.66, 146.99, 147.82, 148.03, 148.60; IR (neat) 2957 (s), 2933 (s), 1589 (w), 1543 (s), 1516 (s), 1455 (w), 1337 (s), 1261 (s), 1236 (s), 1029 (s) cm−1; HRMS (FAB) m/z calcd for C26H34N3O6 (M+H)+: 484.2448. found: 484.2444.

Workup

  1. customAfter workup and purification with column chromatography (80% EtOAc in hexanes as eluant)

Sources & evidence

ORD record
ord-3d664d8e75004b00b0698f61a81da437
Source dataset
uspto-grants-2015_07
Patent number
US09084779B2

Reaction notes

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